(Z)-1-(tert-butoxycarbonyl)-3-[(E)-4-tert-butoxycarbonylamino-6-phenylhex-5-en-2-ylidene]indolin-2-one | 1537870-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (Z)-1-(tert-butoxycarbonyl)-3-[(E)-4-tert-butoxycarbonylamino-6-phenylhex-5-en-2-ylidene]indolin-2-one
• 英文别名: tert-butyl (3Z)-3-[(E)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhex-5-en-2-ylidene]-2-oxoindole-1-carboxylate
• CAS: 1537870-04-4
• 化学式: C₃₀H₃₆N₂O₅
• 分子量: 504.626
• InChiKey: QFUYUEVGAILXGQ-MMVPFZDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]-3-(prop-1-en-2-yl)-1H-indole 、 di-tert-butyl ((E)-3-phenylprop-2-ene-1,1-diyl)dicarbamate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以56%的产率得到(Z)-1-(tert-butoxycarbonyl)-3-[(E)-4-tert-butoxycarbonylamino-6-phenylhex-5-en-2-ylidene]indolin-2-one
  参考文献：
  名称：

  3-Alkenyl-2-silyloxyindoles in Vinylogous Mannich Reactions: Synthesis of Aminated Indole-Based Scaffolds and Products

  摘要：

  The first Lewis acid catalyzed vinylogous Mukaiyama-type Mannich addition of 3-alkenyl-2-silyloxyindoles to in situ generated N-Boc imines has been established, which affords chiral alpha-alkylidene-delta-amino-2-oxindole products with good efficiency and complete gamma-site- and Z-selectivity. The reaction is wide in scope, as it can be applied with equal convenience to different silyloxyindole donors and aromatic or aliphatic aminal-derived aldimine acceptors. The utility of these scaffolds is demonstrated by their easy transformation into either spirocyclopropane oxindole,, or homotryptamine-like products, featuring nontraditional indole-based skeleton connections.

  DOI：

  10.1021/ol4036598